N-(tert-butoxycarbonyl)-4-bromo-1-tosyl-D-tryptophan methyl ester | 343846-40-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(tert-butoxycarbonyl)-4-bromo-1-tosyl-D-tryptophan methyl ester
• 英文别名: 4-bromo-1-tosyl-N-(tert-butoxycarbonyl)tryptophan methyl ester；methyl (2R)-3-[4-bromo-1-(4-methylphenyl)sulfonylindol-3-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 343846-40-2
• 化学式: C₂₄H₂₇BrN₂O₆S
• 分子量: 551.458
• InChiKey: YCLPLEOYNXJYGR-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-4-bromo-1-tosyl-D-tryptophan methyl ester 在 氢氧化钾 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.5h， 生成 (2R)-3-[4-bromo-1-(4-methylphenyl)sulfonylindol-3-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
  参考文献：
  名称：

  An Efficient Method of Synthesizing Optically Pure N-Boc-4-bromo-N-methyl-1-tosyl-D-tryptophan Methyl Ester, a Key Intermediate in the Synthesis of Optically Active Ergot Alkaloids

  摘要：

  Optically pure N-Boc-4-bromo-N-methyl-1-tosyl-D-tryptophan methyl ester (D-4), a key intermediate in the synthesis of optically active ergot alkaloids such as chanoclavine-I (7) and costaclavine (8), was prepared from N-acetyl-4-bromo-D-tryptophan (D-ll) obtained from 4-bromoindole (9) and DL-serine (10) in two steps.

  DOI：

  10.3987/com-00-9137
• 作为产物：
  描述：

  2-叔丁氧羰基氨基丙烯酸甲酯 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate palladium diacetate 、 1,2-乙烷二基二[(2-甲氧基苯基)(苯基)膦] 、 氢气 、 四氯苯醌 、 碳酸氢钠 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 25.0~83.0 ℃ 、405.3 kPa 条件下， 反应 104.0h， 生成 N-(tert-butoxycarbonyl)-4-bromo-1-tosyl-D-tryptophan methyl ester
  参考文献：
  名称：

  Optically Active Total Synthesis of Clavicipitic Acid

  摘要：

  DOI：

  10.1021/jo00111a004

文献信息

• Enantioselective Synthesis of (+)-Isolysergol via Ring-Closing Metathesis
  作者：Jason A. Deck、Stephen F. Martin

  DOI：10.1021/ol100819f

  日期：2010.6.4

  The first enantioselective synthesis of (+)-isolysergol was completed in 12 steps from commercially available materials by a novel approach that features a late stage microwave-mediated, diastereomeric ring-closing metathesis catalyzed by a chiral molybdenum catalyst to simultaneously form the D ring and set the stereocenter at C(8).
• Optically Active Total Synthesis of Clavicipitic Acid
  作者：Yuusaku Yokoyama、Toshifumi Matsumoto、Yasuoki Murakami

  DOI：10.1021/jo00111a004

  日期：1995.3
• An Efficient Method of Synthesizing Optically Pure N-Boc-4-bromo-N-methyl-1-tosyl-D-tryptophan Methyl Ester, a Key Intermediate in the Synthesis of Optically Active Ergot Alkaloids
  作者：Yuusaku Yokoyama、Kumi Osanai、Masaharu Mitsuhashi、Kazuhiro Kondo、Yasuoki Murakami

  DOI：10.3987/com-00-9137

  日期：——

  Optically pure N-Boc-4-bromo-N-methyl-1-tosyl-D-tryptophan methyl ester (D-4), a key intermediate in the synthesis of optically active ergot alkaloids such as chanoclavine-I (7) and costaclavine (8), was prepared from N-acetyl-4-bromo-D-tryptophan (D-ll) obtained from 4-bromoindole (9) and DL-serine (10) in two steps.